Iprodione | CAS#36734-19-7 | fungicide

MedKoo Cat#: 558511 | Name: Iprodione

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Iprodione is a fungicide, bactericide, and wood preservative.

Chemical Structure

Iprodione

CAS#36734-19-7

Theoretical Analysis

MedKoo Cat#: 558511

Name: Iprodione

CAS#: 36734-19-7

Chemical Formula: C13H13Cl2N3O3

Exact Mass: 329.0334

Molecular Weight: 330.17

Elemental Analysis: C, 47.29; H, 3.97; Cl, 21.47; N, 12.73; O, 14.54

Price and Availability

Size	Price	Availability	Quantity
1g	USD 350.00	2 Weeks
5g	USD 850.00	2 Weeks

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Synonym

Iprodione; Glycophen; Glycophene;

IUPAC/Chemical Name

1-Imidazolidinecarboxamide, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-

InChi Key

ONUFESLQCSAYKA-UHFFFAOYSA-N

InChi Code

InChI=1S/C13H13Cl2N3O3/c1-7(2)16-12(20)17-6-11(19)18(13(17)21)10-4-8(14)3-9(15)5-10/h3-5,7H,6H2,1-2H3,(H,16,20)

SMILES Code

O=C(N(C(N1C2=CC(Cl)=CC(Cl)=C2)=O)CC1=O)NC(C)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Iprodione, a dicarboximide fungicide, has a highly specific action, with a capacity to cause oxidative damage through production of free oxygen radicals (ROS). Iprodione does not appear to be species selective.

In vitro activity:

In this study, a cocktail of seven pesticides frequently present in water and food (maneb, mancozeb, iprodione, imazalil, chlorpyrifos ethyl, diazinon and dimethoate), as determined by the European Food Safety Authority, were selected. Exposure of normal BM-MSCs to pesticides for 21 days inhibited cell proliferation and promoted DNA damage and senescence. Concomitantly, these cells presented a decrease in aldehyde dehydrogenase 2 (ALDH2: mRNA, protein and enzymatic activity) and an increase in acetaldehyde levels. Reference: Cancers (Basel). 2021 Nov 14;13(22):5699. https://pubmed.ncbi.nlm.nih.gov/34830855/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	302.88

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 330.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Foucault A, Ravalet N, Besombes J, Picou F, Gallay N, Babin L, Bourgeais J, Hamard S, Domenech J, Loyer P, Vallet N, Lejeune J, Gyan E, Béné MC, Vallette F, Olivier C, Hérault O. Low-Dose Pesticides Alter Primary Human Bone Marrow Mesenchymal Stem/Stromal Cells through ALDH2 Inhibition. Cancers (Basel). 2021 Nov 14;13(22):5699. doi: 10.3390/cancers13225699. PMID: 34830855; PMCID: PMC8616329. 2. Maqsood A, Wu C, Ahmar S, Wu H. Cytological and Gene Profile Expression Analysis Reveals Modification in Metabolic Pathways and Catalytic Activities Induce Resistance in Botrytis cinerea Against Iprodione Isolated From Tomato. Int J Mol Sci. 2020 Jul 9;21(14):4865. doi: 10.3390/ijms21144865. PMID: 32660143; PMCID: PMC7402349.

In vitro protocol:

In vivo protocol:

TBD

1: Lassalle Y, Jellouli H, Ballerini L, Souissi Y, Nicol É, Bourcier S, Bouchonnet S. Ultraviolet-vis degradation of iprodione and estimation of the acute toxicity of its photodegradation products. J Chromatogr A. 2014 Dec 5;1371:146-53. doi: 10.1016/j.chroma.2014.10.051. Epub 2014 Oct 24. PubMed PMID: 25456592. 2: Grabke A, Fernández-Ortuño D, Amiri A, Li X, Peres NA, Smith P, Schnabel G. Characterization of iprodione resistance in Botrytis cinerea from strawberry and blackberry. Phytopathology. 2014 Apr;104(4):396-402. doi: 10.1094/PHYTO-06-13-0156-R. PubMed PMID: 24156554. 3: Galli CL, Sensi C, Fumagalli A, Parravicini C, Marinovich M, Eberini I. A computational approach to evaluate the androgenic affinity of iprodione, procymidone, vinclozolin and their metabolites. PLoS One. 2014 Aug 11;9(8):e104822. doi: 10.1371/journal.pone.0104822. eCollection 2014. PubMed PMID: 25111804; PubMed Central PMCID: PMC4128724. 4: Wang X, Xu G, Wang F, Sun H, Li Y. Iprodione residues and dissipation rates in tobacco leaves and soil. Bull Environ Contam Toxicol. 2012 Oct;89(4):877-81. doi: 10.1007/s00128-012-0783-8. Epub 2012 Aug 15. PubMed PMID: 22893179. 5: Verdenelli RA, Lamarque AL, Meriles JM. Short-term effects of combined iprodione and vermicompost applications on soil microbial community structure. Sci Total Environ. 2012 Jan 1;414:210-9. doi: 10.1016/j.scitotenv.2011.10.066. Epub 2011 Nov 23. PubMed PMID: 22115616. 6: Morales J, Manso JA, Cid A, Mejuto JC. Stability study of Iprodione in alkaline media in the presence of humic acids. Chemosphere. 2013 Sep;92(11):1536-41. doi: 10.1016/j.chemosphere.2013.04.020. Epub 2013 May 16. PubMed PMID: 23683355. 7: Fillinger S, Ajouz S, Nicot PC, Leroux P, Bardin M. Functional and structural comparison of pyrrolnitrin- and iprodione-induced modifications in the class III histidine-kinase Bos1 of Botrytis cinerea. PLoS One. 2012;7(8):e42520. doi: 10.1371/journal.pone.0042520. Epub 2012 Aug 13. PubMed PMID: 22912706; PubMed Central PMCID: PMC3418262. 8: Pisani C, Voisin S, Arafah K, Durand P, Perrard MH, Guichaoua MR, Bulet P, Prat O. Ex vivo assessment of testicular toxicity induced by carbendazim and iprodione, alone or in a mixture. ALTEX. 2016;33(4):393-413. doi: 10.14573/altex.1601253. Epub 2016 May 8. PubMed PMID: 27155993. 9: Maeda O, Oikawa C, Noguchi K, Shiomi N, Toriba A, Hayakawa K. Quantification of iprodione in dry basil using silica gel supported titanium dioxide. J Agric Food Chem. 2010 Feb 10;58(3):1416-9. doi: 10.1021/jf9032798. PubMed PMID: 20000573. 10: Leistra M, Matser AM. Adsorption, transformation, and bioavailability of the fungicides carbendazim and iprodione in soil, alone and in combination. J Environ Sci Health B. 2004 Jan;39(1):1-17. PubMed PMID: 15022737. 11: Athiel P, Alfizar, Mercadier C, Vega D, Bastide J, Davet P, Brunel B, Cleyet-Marel JC. Degradation of iprodione by a soil Arthrobacter-like strain. Appl Environ Microbiol. 1995 Sep;61(9):3216-20. PubMed PMID: 7574630; PubMed Central PMCID: PMC167600. 12: Wang YS, Wen CY, Chiu TC, Yen JH. Effect of fungicide iprodione on soil bacterial community. Ecotoxicol Environ Saf. 2004 Sep;59(1):127-32. PubMed PMID: 15261734. 13: Karaoglanidis GS, Markoglou AN, Bardas GA, Doukas EG, Konstantinou S, Kalampokis JF. Sensitivity of Penicillium expansum field isolates to tebuconazole, iprodione, fludioxonil and cyprodinil and characterization of fitness parameters and patulin production. Int J Food Microbiol. 2011 Jan 31;145(1):195-204. doi: 10.1016/j.ijfoodmicro.2010.12.017. Epub 2010 Dec 28. PubMed PMID: 21251724. 14: Blystone CR, Lambright CS, Cardon MC, Furr J, Rider CV, Hartig PC, Wilson VS, Gray LE Jr. Cumulative and antagonistic effects of a mixture of the antiandrogens vinclozolin and iprodione in the pubertal male rat. Toxicol Sci. 2009 Sep;111(1):179-88. doi: 10.1093/toxsci/kfp137. Epub 2009 Jun 29. PubMed PMID: 19564212. 15: Dierickx PJ. Cytotoxicity of the dicarboximide fungicides, vinclozolin and iprodione, in rat hepatoma-derived Fa32 cells. Altern Lab Anim. 2004 Oct;32(4):369-73. PubMed PMID: 15651921. 16: Washington T, Tchounwou PB. Cytotoxicity and transcriptional activation of stress genes in human liver carcinoma (HepG2) cells exposed to iprodione. Int J Environ Res Public Health. 2004 Mar;1(1):12-20. PubMed PMID: 16696176. 17: Angioni A, Porcu L, Dedola F. Determination of famoxadone, fenamidone, fenhexamid and iprodione residues in greenhouse tomatoes. Pest Manag Sci. 2012 Apr;68(4):543-7. doi: 10.1002/ps.2287. Epub 2011 Nov 18. PubMed PMID: 22102420. 18: Ochiai N, Fujimura M, Oshima M, Motoyama T, Ichiishi A, Yamada-Okabe H, Yamaguchi I. Effects of iprodione and fludioxonil on glycerol synthesis and hyphal development in Candida albicans. Biosci Biotechnol Biochem. 2002 Oct;66(10):2209-15. PubMed PMID: 12450134. 19: Campos M, Karas PS, Perruchon C, Papadopoulou ES, Christou V, Menkissoglou-Spiroudi U, Diez MC, Karpouzas DG. Novel insights into the metabolic pathway of iprodione by soil bacteria. Environ Sci Pollut Res Int. 2017 Jan;24(1):152-163. doi: 10.1007/s11356-016-7682-1. Epub 2016 Oct 5. PubMed PMID: 27704380. 20: Cao L, Shi W, Shu R, Pang J, Liu Y, Zhang X, Lei Y. Isolation and characterization of a bacterium able to degrade high concentrations of iprodione. Can J Microbiol. 2018 Jan;64(1):49-56. doi: 10.1139/cjm-2017-0185. Epub 2017 Dec 8. PubMed PMID: 29219613.